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[ CAS No. 115375-59-2 ] {[proInfo.proName]}

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Chemical Structure| 115375-59-2
Chemical Structure| 115375-59-2
Structure of 115375-59-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 115375-59-2 ]

CAS No. :115375-59-2 MDL No. :N/A
Formula : C12H11F3O4S Boiling Point : -
Linear Structure Formula :CH3OC10H8OSO2CF3 InChI Key :-
M.W : 308.27 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 115375-59-2 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 4
Num. H-bond acceptors : 7.0
Num. H-bond donors : 0.0
Molar Refractivity : 65.73
TPSA : 60.98 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.68
Log Po/w (XLOGP3) : 3.45
Log Po/w (WLOGP) : 5.19
Log Po/w (MLOGP) : 2.05
Log Po/w (SILICOS-IT) : 2.27
Consensus Log Po/w : 3.13

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.88
Solubility : 0.0404 mg/ml ; 0.000131 mol/l
Class : Soluble
Log S (Ali) : -4.41
Solubility : 0.0119 mg/ml ; 0.0000387 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.92
Solubility : 0.0369 mg/ml ; 0.00012 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.93

Safety of [ 115375-59-2 ]

Signal Word:Danger Class:9
Precautionary Statements:P264-P270-P280-P301+P312-P305+P351+P338-P310-P330-P501 UN#:3077
Hazard Statements:H302-H318 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 115375-59-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 115375-59-2 ]

[ 115375-59-2 ] Synthesis Path-Downstream   1~51

  • 1
  • [ 111-34-2 ]
  • [ 115375-59-2 ]
  • 4-(1-butoxyvinyl)-7-methoxy-1,2-dihydronaphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With 1,3-bis-(diphenylphosphino)propane; triethylamine In dimethyl sulfoxide at 40℃; for 20h;
With palladium diacetate; triethylamine In dimethyl sulfoxide at 65℃; for 3h;
  • 2
  • [ 463-49-0 ]
  • [ 115375-59-2 ]
  • [ 112208-96-5 ]
  • [ 57346-12-0 ]
YieldReaction ConditionsOperation in experiment
94% In dimethyl sulfoxide at 70℃; for 72h;
  • 3
  • [ 38352-74-8 ]
  • [ 115375-59-2 ]
  • 1-[5-(6-Methoxy-3,4-dihydro-naphthalen-1-ylmethyl)-2-methyl-furan-3-yl]-ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1.5h;
66% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1.5h;
  • 4
  • [ 115375-59-2 ]
  • [ 115269-99-3 ]
  • [ 130400-07-6 ]
YieldReaction ConditionsOperation in experiment
73% With tetrabutyl-ammonium chloride; potassium acetate In N,N-dimethyl-formamide at 80℃; for 5h;
  • 5
  • [ 115375-59-2 ]
  • [ 143360-93-4 ]
  • 2,2,2-Trifluoro-N-[2-(7-methoxy-3,4-dihydro-naphthalen-1-ylethynyl)-phenyl]-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With copper(l) iodide; diethylamine In N,N-dimethyl-formamide Ambient temperature;
  • 6
  • [ 115375-59-2 ]
  • [ 143360-93-4 ]
  • [ 143360-91-2 ]
YieldReaction ConditionsOperation in experiment
72% With copper(l) iodide; diethylamine In N,N-dimethyl-formamide for 4.5h; Ambient temperature;
  • 7
  • [ 115375-59-2 ]
  • [ 143360-89-8 ]
  • 3-(6-Methoxy-3,4-dihydro-naphthalen-1-yl)-2-phenyl-1H-indole [ No CAS ]
  • 6-Methoxy-3,4-dihydro-naphthalene-1-carboxylic acid (2-phenylethynyl-phenyl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 20% 2: 24% With potassium carbonate In acetonitrile at 45℃;
  • 8
  • [ 115375-59-2 ]
  • [ 143360-89-8 ]
  • 6-Methoxy-3,4-dihydro-naphthalene-1-carboxylic acid (2-phenylethynyl-phenyl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With potassium carbonate In acetonitrile at 45℃;
  • 9
  • [ 115375-59-2 ]
  • [ 143360-90-1 ]
  • [ 143360-85-4 ]
YieldReaction ConditionsOperation in experiment
89% With potassium carbonate In acetonitrile for 48h; Ambient temperature;
89% With potassium carbonate In acetonitrile at 20℃; for 3h;
  • 10
  • [ 115375-59-2 ]
  • [ 109-92-2 ]
  • [ 118716-36-2 ]
YieldReaction ConditionsOperation in experiment
56% With palladium diacetate; triethylamine In dimethyl sulfoxide at 60 - 65℃; for 3h;
  • 11
  • [ 115375-59-2 ]
  • [ 927-74-2 ]
  • [ 151171-91-4 ]
YieldReaction ConditionsOperation in experiment
86% With diethylamine In N,N-dimethyl-formamide for 4h; Ambient temperature;
  • 12
  • [ 358-23-6 ]
  • [ 1078-19-9 ]
  • [ 115375-59-2 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine In dichloromethane at 0 - 40℃; for 24h; Sealed tube; Inert atmosphere; General Procedure B: Synthesis of Trifluoromethanesulfonates General procedure: To an oven dried 25 mL round-bottomed flask was added 1-tetralone (600 mg, 4.1 mmol, 1equiv). The flask was sealed and purged with N2 before addition of CH2Cl2 (16.5 mL, 0.25M) and Et3N (0.86 mL, 6.2 mmol, 1.5 equiv). The reaction mixture was cooled to 0 °C andtrifluoromethanesulfonic anhydride (1 mL, 6.2 mmol, 1.5 equiv) was added dropwise undernitrogen before it was heated to 40 °C and maintained at this temperature with stirring for 24h. Upon completion of the reaction, the solution was washed with water (2 x 20 mL) and theorganics passed through a hydrophobic frit and concentrated under reduced pressure to give abrown oil, which was purified by flash chromatography (silica gel, 0-5% Et2O in petroleumether) to afford the title compound as a yellow oil (1.15 g, quant.).
70% Stage #1: 6-methoxy-3,4-dihydro-1(2H)-naphthalenone With triethylamine In dichloromethane at 0℃; for 0.166667h; Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at 0 - 20℃;
69% With triethylamine In dichloromethane at 0℃; for 22h; Inert atmosphere; Reflux; 2.1. General Procedure A: Triflation of tetralones General procedure: For example, the preparation of 6-methoxy-3,4-dihydronaphthalen-1-yl trifluoromethanesulfonate (1a)-6-Methoxy-1-tetralone (2.00 g, 11.35 mmol, 1 equiv) was weighed into an oven-dried flask.The flask was sealed and purged with N2 before the addition of CH2Cl2 (45 mL, 0.25 M). The reaction was cooled to 0 °C and triflic anhydride (3.8 mL, 22.7 mmol, 2 equiv) and Et3N (3.2mL, 22.7 mmol, 2 equiv) were added dropwise via syringe sequentially. The reaction mixture was then heated to reflux for 22 h with stirring. After the reaction was complete, the reaction was allowed to cool to room temperature and concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel, 0-5% EtOAc in petroleum ether)to afford the desired product as a yellow oil (2.41 g, 69%).
62% With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane for 7h; Ambient temperature;
With Cs2CO3 In 1,4-dioxane; toluene regioselective reaction;
Stage #1: 6-methoxy-3,4-dihydro-1(2H)-naphthalenone With 2-chloropyridine In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at 0 - 20℃; Inert atmosphere;

  • 13
  • [ 65763-00-0 ]
  • [ 201230-82-2 ]
  • [ 115375-59-2 ]
  • 6-Methoxy-3,4-dihydro-naphthalene-1-carboxylic acid 8-iodo-2-oxo-2H-chromen-7-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With potassium carbonate In acetonitrile Ambient temperature;
  • 14
  • [ 201230-82-2 ]
  • [ 16188-57-1 ]
  • [ 115375-59-2 ]
  • [ 170744-92-0 ]
YieldReaction ConditionsOperation in experiment
88% With potassium carbonate In acetonitrile Ambient temperature;
  • 15
  • [ 201230-82-2 ]
  • [ 71643-66-8 ]
  • [ 115375-59-2 ]
  • 6-Methoxy-3,4-dihydro-naphthalene-1-carboxylic acid 4-chloro-2-iodo-phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With potassium carbonate In acetonitrile Ambient temperature;
  • 16
  • [ 201230-82-2 ]
  • [ 2713-29-3 ]
  • [ 115375-59-2 ]
  • 6-Methoxy-3,4-dihydro-naphthalene-1-carboxylic acid 4-fluoro-2-iodo-phenyl ester [ No CAS ]
  • 17
  • [ 201230-82-2 ]
  • [ 71031-48-6 ]
  • [ 115375-59-2 ]
  • 6-Methoxy-3,4-dihydro-naphthalene-1-carboxylic acid 3-iodo-biphenyl-4-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With potassium carbonate In acetonitrile Ambient temperature;
  • 18
  • [ 201230-82-2 ]
  • [ 170744-87-3 ]
  • [ 115375-59-2 ]
  • 6-Methoxy-3,4-dihydro-naphthalene-1-carboxylic acid 4-benzoyl-2-iodo-phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With potassium carbonate In acetonitrile Ambient temperature;
  • 19
  • [ 37595-74-7 ]
  • [ 1078-19-9 ]
  • [ 115375-59-2 ]
YieldReaction ConditionsOperation in experiment
100% Stage #1: 6-methoxy-3,4-dihydro-1(2H)-naphthalenone With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.75h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 0℃; for 3h;
89% With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 16h; Inert atmosphere;
80% Stage #1: 6-methoxy-3,4-dihydro-1(2H)-naphthalenone With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
38% Stage #1: 6-methoxy-3,4-dihydro-1(2H)-naphthalenone With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at 20℃; Inert atmosphere; 30.1 Step 1. 6-methoxy-3 ,4-dihydronaphthalen- 1 -yl trifluoromethanesulfonate Into a 50-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 6-methoxy- 1,2,3 ,4-tetrahydronaphthalen- 1-one (500 mg, 2.84 mmol, 1.00 equiv) in tetrahydrofuran (14 mL). This was followed by the addition of LHIVIDS (1M in tetrahydrofuran) (4.3 mL) at -78 °C. The mixture was stirred for lh at -78 °C. To this was added phenyl [(trifluoromethane) sulfonyloxy] amino trifluoromethanesulfonate (1.52 g, 3.90 mmol, 1.90 equiv). The resulting solution was stirred overnight at room temperature (20 °C). The resulting solution was diluted with 40 mL of EA, washed with brine (100 mL x 2) and of sat. NH4C1 (100 mL x 2), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was applied onto a silica gel column with EA:PE (0-10%). The collected fraction was concentrated to give 330 mg (38%) of 6-methoxy-3,4- dihydronaphthalen-1-yl trifluoromethanesulfonate as a yellow solid. MS (ES, m/z): 309 [M+H]
With lithium hexamethyldisilazane 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C to RT, 1 h; Yield given. Multistep reaction;
Stage #1: 6-methoxy-3,4-dihydro-1(2H)-naphthalenone With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 20℃; for 2h;
Stage #1: 6-methoxy-3,4-dihydro-1(2H)-naphthalenone With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
Stage #1: 6-methoxy-3,4-dihydro-1(2H)-naphthalenone With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.666667h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 0℃; for 3h;

  • 20
  • [ 623-43-8 ]
  • [ 115375-59-2 ]
  • (E)-3-(6-Methoxy-3,4-dihydro-naphthalen-1-yl)-but-2-enoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With palladium diacetate; potassium acetate In N,N-dimethyl-formamide at 60℃; for 24h;
  • 21
  • [ 463-49-0 ]
  • [ 115375-59-2 ]
  • [ 57346-12-0 ]
  • 1-isopropenyl-6-methoxynaphthalene [ No CAS ]
  • [ 183194-89-0 ]
YieldReaction ConditionsOperation in experiment
1: 94% 2: 16.5% 3: 5% With 2-Methylcyclopentane-1,3-dione; sodium hydride; triphenylphosphine; lithium chloride; bis(dibenzylideneacetone)-palladium(0) In dimethyl sulfoxide at 65℃; for 76h;
  • 22
  • [ 764-48-7 ]
  • [ 115375-59-2 ]
  • 2-(3,4-dihydro-6-methoxy-1-naphthyl)-2-methyl-1,3-dioxolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With 1,3-bis-(diphenylphosphino)propane; triethylamine In dimethyl sulfoxide for 0.0833333h; Irradiation;
  • 23
  • [ 115375-59-2 ]
  • [ 328077-61-8 ]
  • Acetic acid 2-[(Z)-3-hydroxy-1-(6-methoxy-3,4-dihydro-naphthalen-1-yl)-3-methyl-but-1-enyl]-4-methyl-phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With palladium diacetate; potassium formate In N,N-dimethyl-formamide at 40℃; for 6h;
  • 24
  • [ 547-65-9 ]
  • [ 115375-59-2 ]
  • α-(6-methoxytetrahydronaphth-1-yl)methyl-γ-butyrolactone [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: α-methylene-γ-butyrolactone; 6-methoxy-3,4-dihydronaphthalene-1-yl triflate With potassium acetate In N,N-dimethyl-formamide at 80℃; for 6h; Stage #2: With hydrogen In ethyl acetate for 3h; Further stages.;
  • 25
  • [ 88-12-0 ]
  • [ 115375-59-2 ]
  • 1-[1-(6-methoxy-3,4-dihydro-1-naphthalenyl)vinyl]-2-pyrrolidinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine In dimethyl sulfoxide at 70℃; for 18h;
  • 26
  • [ 2235-00-9 ]
  • [ 115375-59-2 ]
  • 1-[1-(6-methoxy-3,4-dihydro-1-naphthalenyl)vinyl]-2-azepanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine In dimethyl sulfoxide at 70℃; for 18h;
  • 27
  • [ 3195-78-6 ]
  • [ 115375-59-2 ]
  • N-[1-(6-methoxy-3,4-dihydro-1-naphthalenyl)vinyl]-N-methylacetamide [ No CAS ]
  • 28
  • [ 556-63-8 ]
  • [ 115375-59-2 ]
  • [ 198068-77-8 ]
  • 30
  • [ 3622-76-2 ]
  • [ 115375-59-2 ]
  • (Z)-{2-[2-(6-methoxy-3,4-dihydronaphthalen-1-yl)-vinyloxy]-ethyl}-dimethylamine [ No CAS ]
  • (E)-{2-[2-(6-methoxy-3,4-dihydronaphthalen-1-yl)-vinyloxy]-ethyl}-dimethylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triphenylphosphine In dimethyl sulfoxide at 60℃; for 24h;
  • 31
  • [ 3205-13-8 ]
  • [ 115375-59-2 ]
  • (Z)-{2-[2-(6-methoxy-3,4-dihydronaphthalen-1-yl)-vinyloxy]-ethyl}-diethylamine [ No CAS ]
  • (E)-{2-[2-(6-methoxy-3,4-dihydronaphthalen-1-yl)-vinyloxy]-ethyl}-diethylamine [ No CAS ]
  • diethyl-{2-[1-(6-methoxy-3,4-dihydro-naphthalen-1-yl)-vinyloxy]-ethyl}-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tri tert-butylphosphoniumtetrafluoroborate In dimethyl sulfoxide at 60℃; for 24h; Title compound not separated from byproducts;
  • 32
  • [ 115375-59-2 ]
  • [ 53135-09-4 ]
  • (E)-2-[2-(6-methoxy-3,4-dihydronaphthalen-1-yl)-vinyloxymethyl]-1-methyl-pyrrolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With triphenylphosphine In dimethyl sulfoxide at 80℃; for 48h;
  • 33
  • [ 123-75-1 ]
  • [ 115375-59-2 ]
  • [ 199620-15-0 ]
  • [ 1189371-46-7 ]
YieldReaction ConditionsOperation in experiment
73% With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; XPhos In tetrahydrofuran at 80℃; for 0.333333h; Inert atmosphere; Microwave irradiation;
  • 34
  • [ 111-26-2 ]
  • [ 115375-59-2 ]
  • [ 199620-15-0 ]
  • [ 1189371-44-5 ]
YieldReaction ConditionsOperation in experiment
62% With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; XPhos In tetrahydrofuran at 60℃; for 0.333333h; Inert atmosphere; Microwave irradiation;
  • 35
  • [ 115375-59-2 ]
  • [ 62-53-3 ]
  • [ 199620-15-0 ]
  • [ 1189371-45-6 ]
YieldReaction ConditionsOperation in experiment
78% With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; XPhos In tetrahydrofuran at 80℃; for 0.333333h; Inert atmosphere; Microwave irradiation;
  • 36
  • [ 115375-59-2 ]
  • [ 100-46-9 ]
  • [ 199620-15-0 ]
  • [ 1189371-43-4 ]
YieldReaction ConditionsOperation in experiment
73% With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 60℃; for 0.333333h; Inert atmosphere; Microwave irradiation;
  • 37
  • [ 115375-59-2 ]
  • [ 13139-86-1 ]
  • [ 79822-57-4 ]
YieldReaction ConditionsOperation in experiment
70% With iron(III) chloride; copper(I) thiophene-2-carboxylate In tetrahydrofuran at -20 - 20℃; for 2h; Inert atmosphere;
  • 38
  • [ 67-56-1 ]
  • hydroxycarbene [ No CAS ]
  • [ 115375-59-2 ]
  • methyl 6-methoxy-3,4-dihydronaphthalene-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 65℃; for 16h; Inert atmosphere;
  • 39
  • [ 13331-27-6 ]
  • [ 115375-59-2 ]
  • 7-methoxy-4-(3-nitrophenyl)-1,2-dihydronaphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In water; N,N-dimethyl-formamide at 130℃; for 0.5h; Inert atmosphere;
  • 40
  • bis(tetrahydrofuran)tris(trimethylsilylmethyl)yttrium(III) [ No CAS ]
  • [ 115375-59-2 ]
  • C15H22OSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With tetrakis(triphenylphosphine) palladium(0) In toluene at 20℃; for 0.75h; Schlenk technique; Inert atmosphere;
  • 41
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 115375-59-2 ]
  • methyl 6-methoxy-3,4-dihydronaphthalene-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine at 120℃; Inert atmosphere; 30.2 Step 2. Methyl 6-methoxy-3 ,4-dihydronaphthalene- 1 -carboxylate Into a 30-mL pressure tank reactor (60 atm) purged and maintained with an inert atmosphere of CO, was placed 6-methoxy-3,4-dihydronaphthalen-1-yl trifluoromethanesulfonate (300 mg, 0.97 mmol, 1.00 equiv), Pd(dppf)C12CH2C12 (400 mg, 0.49 mmol, 0.50 equiv), TEA (492 mg,4.86 mmol, 5.00 equiv), MeOH (8 mL). The resulting solution was stirred overnight at 120°C. The resulting solution was cooled to 25 °C. The solids were filtered out. The filtrate was concentrated under vacuum. The crude product was purified by Prep-TLC with ethyl acetate/petroleum ether (1/12). This resulted in 170 mg (80%) of methyl 6-methoxy-3,4- dihydronaphthalene-1-carboxylate as yellow oil. MS (ES, m/z): 219 [M+H]
  • 42
  • [ 115375-59-2 ]
  • [ 80858-95-3 ]
  • 43
  • [ 327-54-8 ]
  • [ 115375-59-2 ]
  • C17H12F4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With bis(1,5-cyclooctadiene)nickel (0); 18-crown-6 ether; 2-[bis((3,5-dimethyl-4-methoxyphenyl)phosphino)phenyl]ether; isopropylmagnesium chloride In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane at 40℃; for 2h;
  • 44
  • [ 941-69-5 ]
  • [ 115375-59-2 ]
  • [ 75927-49-0 ]
  • C23H21NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% Stage #1: 6-methoxy-3,4-dihydronaphthalene-1-yl triflate; pinacol vinylboronate With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane; water at 50℃; for 1h; Inert atmosphere; Sealed tube; Stage #2: N-phenyl-maleimide In 1,4-dioxane; water at 20℃; for 24h; Inert atmosphere; Sealed tube;
  • 45
  • [ 5720-05-8 ]
  • [ 115375-59-2 ]
  • 7-methoxy-4-(p-tolyl)-1,2-dihydronaphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 50℃; for 5h; Inert atmosphere; General Procedure for Suzuki-Miyaura Coupling in Cyrene General procedure: To an oven dried 5 mL microwave vessel was addedPd(dppf)Cl2·CH2Cl2 (4 mol%), halide/pseudohalide (1 equiv),boron coupling partner (1 equiv), and Cs2CO3 (3 equiv). Thevessel was then capped and purged with N2 before addition ofCyrene (1 mL, 0.25 M) and H2O (1.8 mL). The reaction mixturewas heated to 50 °C and maintained at this temperature withstirring for 5 h before the vessel was vented and decapped. Thesolution was then diluted with Et2O (10 mL) and washed withwater (2 × 20 mL) and brine (2 × 20 mL). The organics were thenpassed through a hydrophobic frit and concentrated underreduced pressure to give a residue, which was purified by flashchromatography (silica gel) to afford the title compound.
  • 46
  • [ 115375-59-2 ]
  • [ 75927-49-0 ]
  • C21H29BO3 [ No CAS ]
  • C21H29BO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 6-methoxy-3,4-dihydronaphthalene-1-yl triflate; pinacol vinylboronate With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane; water at 50℃; for 1h; Inert atmosphere; Sealed tube; Stage #2: In 1,4-dioxane; water at 150℃; for 23h; Inert atmosphere; Sealed tube; 2.4. General Procedure D: SM/DA optimization protocol for tricyclic system General procedure: For example the preparation of 3a/3a’- Pd(OAc)2 (2.2 mg, 0.01 mmol, 4 mol%), SPhos (8.2 mg, 0.02 mmol, 8 mol%), 6-methoxy-3,4-dihydronaphthalen-1-yl trifluoromethanesulfonate (77.0 mg, 0.25 mmol, 1 equiv), vinylBpin (192 mg, 1.25 mmol, 5 equiv) and K3PO4 (159 mg, 0.75 mmol, 3 equiv) were weighed into an oven dried microwave vial. The reaction vessel was then capped and purged with N2 before the addition of 1,4-dioxane (2 mL, 0.125 M) and H2O (22.5 μl, 1.25 mmol, 5 equiv).The reaction mixture was heated to 50 °C with stirring. After 1 h the temperature was increased to 150 °C, and the reaction mixture was stirred for 23 h. After the reaction was complete, the reaction mixture was allowed to cool to room temperature and was vented and de-capped. The reaction mixture was diluted in EtOAc (20 mL) and passed through a layer of celite. Conversion to the desired product was measured by 1H NMR against a known internal standard (dibenzyl ether).
  • 47
  • [ 115375-59-2 ]
  • [ 75927-49-0 ]
  • [ 2811-50-9 ]
YieldReaction ConditionsOperation in experiment
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane; water at 50℃; for 1h; Inert atmosphere; Sealed tube; 2.4. General Procedure D: SM/DA optimization protocol for tricyclic system General procedure: For example the preparation of 3a/3a’- Pd(OAc)2 (2.2 mg, 0.01 mmol, 4 mol%), SPhos (8.2 mg, 0.02 mmol, 8 mol%), 6-methoxy-3,4-dihydronaphthalen-1-yl trifluoromethanesulfonate (77.0 mg, 0.25 mmol, 1 equiv), vinylBpin (192 mg, 1.25 mmol, 5 equiv) and K3PO4 (159 mg, 0.75 mmol, 3 equiv) were weighed into an oven dried microwave vial. The reaction vessel was then capped and purged with N2 before the addition of 1,4-dioxane (2 mL, 0.125 M) and H2O (22.5 μl, 1.25 mmol, 5 equiv).The reaction mixture was heated to 50 °C with stirring. After 1 h the temperature was increased to 150 °C, and the reaction mixture was stirred for 23 h. After the reaction was complete, the reaction mixture was allowed to cool to room temperature and was vented and de-capped. The reaction mixture was diluted in EtOAc (20 mL) and passed through a layer of celite. Conversion to the desired product was measured by 1H NMR against a known internal standard (dibenzyl ether).
  • 48
  • [ 115375-59-2 ]
  • [ 75927-49-0 ]
  • C15H18O2 [ No CAS ]
  • C15H18O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 6-methoxy-3,4-dihydronaphthalene-1-yl triflate; pinacol vinylboronate With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane; water at 50℃; for 1h; Inert atmosphere; Sealed tube; Stage #2: In 1,4-dioxane; water at 150℃; for 23h; Inert atmosphere; Sealed tube; Stage #3: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 1h; Overall yield = 72 %; Overall yield = 41.3 mg; regioselective reaction; 2.5. General Procedure E: SM/DA/oxidation protocol General procedure: For example the preparation of 4a- Pd(OAc)2 (2.2 mg, 0.01 mmol, 4 mol%), SPhos (8.2 mg, 0.02 mmol, 8 mol%), 6-methoxy-3,4-dihydronaphthalen-1-yl trifluoromethanesulfonate (77.0 mg, 0.25 mmol, 1 equiv), vinyl Bpin (192 mg, 1.25 mmol, 5 equiv) and K3PO4 (159 mg, 0.75 mmol, 3 equiv) were weighed into an oven dried microwave vial. The reaction vessel was then capped and purged with N2 before the addition of 1,4-dioxane (2 mL, 0.125 M) and H2O (22.5 μl, 1.25 mmol, 5 equiv).The reaction mixture was heated to 50 °C with stirring. After 1 h the temperature was increased to 150 °C, and the reaction mixture was stirred for 23 h. After the reaction was complete, the reaction mixture was allowed to cool to room temperature and was vented and de-capped. The reaction mixture was diluted in EtOAc (20 mL) and passed through a layer of celite, and concentrated under reduced pressure. THF (1 mL, 0.25 M) was added to the crude residue and the solution was cooled to 0 °C before the addition of aqueous H2O2 (30% w/v,500 μL, 5 mmol, 20 equiv) and 2 M NaOH (500 μL, 1 mmol, 4 equiv) sequentially. After 5 min the reaction mixture was allowed to warm to room temperature and was stirred for 1 h.After the reaction was complete, the mixture was quenched with Na2S2O3 at 0 °C until effervescence ceases and was subsequently diluted in saturated aqueous NH4Cl (25 mL).Organics were extracted with EtOAc (3 × 20 mL), washed with brine (20 mL), dried overNa2SO4, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel, 0-60% EtOAc in petroleum ether) to afford the desired product as a yellow oil (41.3 mg, 72%, 3:1 r.r.).
  • 49
  • [ 115375-59-2 ]
  • [ 75927-49-0 ]
  • (E)-2-(2-(6-methoxy-3,4-dihydronaphthalen-1-yl)vinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; silver(I) acetate; palladium diacetate; triethylamine In 1,4-dioxane at 40℃; for 24h; Inert atmosphere; Sealed tube; (E)-2-(2-(6-Methoxy-3,4-dihydronaphthalen-1-yl)vinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (6a) Pd(OAc)2 (2.2 mg, 0.01 mmol, 4 mol%), SPhos (8.2 mg, 0.02 mmol, 8 mol%), 6-methoxy-3,4-dihydronaphthalen-1-yl trifluoromethanesulfonate (77.0 mg, 0.25 mmol, 1 equiv), vinylBpin (76.9 mg, 0.5 mmol, 2 equiv) and AgOAc (83.4 mg, 0.5 mmol, 2 equiv) were weighed into an oven dried microwave vial. The reaction vessel was then capped and purged with N2 before the addition of 1,4-dioxane (1 mL, 0.25 M) and distilled Et3N (104 μL, 0.75 mmol, 3equiv). The reaction mixture was heated to 40 °C and with stirring for 24 h. After the reaction was complete, the reaction mixture was allowed to cool to room temperature and was vented and de-capped. The reaction mixture was diluted in EtOAc (20 mL) and passed through a layer of celite. The mixture was then washed with H2O (3 × 20 mL) and separated. The combined organics were washed with brine (20 mL), before being dried over Na2SO4,filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel, 0-5% EtOAc in petroleum ether) to afford the desired product as a yellow oil (24.8 mg, 32%). Product is highly air sensitive and was used immediately in subsequent reactions.
  • 50
  • [ 15159-40-7 ]
  • [ 1663-39-4 ]
  • [ 115375-59-2 ]
  • tert-butyl (E)-3-(6-methoxy-2-(morpholine-4-carbonyl)-3,4-dihydronaphthalen-1-yl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With bis[(2,2,2-trifluoroacetyl)oxy]palladium; 5-phenyl-5H-benzo[b]phosphindole; C15H25NO; Cs2CO3 In toluene at 100℃; for 8h; Inert atmosphere; Sealed tube;
  • 51
  • [ 115375-59-2 ]
  • [ 25015-63-8 ]
  • 2-(6-methoxy-3,4-dihydronaphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With Chromium (III) chloride; magnesium; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 20℃; for 24h; Schlenk technique; Inert atmosphere; chemoselective reaction;
Same Skeleton Products
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